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HCID 6072Erstellt: 26. Oktober 2026

2'-(beta-D-Glucopyranosyloxy)-4,'6'-dihydroxy-3-(4-hydroxyphe-nyl)propiophenon

PHLORIDZIN · phlorhizin · phlorizine · phloridzine · PHLORIDZIN DIHYDRATE · NSC 2833 · Floridzin · PHLORIZIN

https://huagongshe.com/de/chemical/6072

Molekülstruktur von 2'-(beta-D-Glucopyranosyloxy)-4,'6'-dihydroxy-3-(4-hydroxyphe-nyl)propiophenon

Identifikatoren & physikalische Daten

CAS No.60-81-1
SummenformelC21H24O10
Durchschnittliche Molmasse436,4 g/mol
Monoisotopische Masse436,13694697 g/mol
SMILESO=C(CCc1ccc(O)cc1)c1c(O)cc(O)cc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChIKeyIOUVKUPGCMBWBT-QNDFHXLGSA-N
PubChem CID6072
ChEMBLCHEMBL245067
ChEBICHEBI:8113
DTXSIDDTXSID3075339
Lokaler Name2'-(beta-D-Glucopyranosyloxy)-4,'6'-dihydroxy-3-(4-hydroxyphe-nyl)propiophenon

Chemische & physikalische Eigenschaften

XLogP1,2
Polarare Oberfläche (TPSA)177
H-Brücken-Donoren7
H-Brücken-Akzeptoren10
Frei drehbare Bindungen7
Schwere Atome31
Formalladung0
Komplexität581
StoffklassenBiological Agents -> Plant Oils and Extracts
LipidePolyketides [PK] -> Flavonoids [PK12] -> Chalcones and dihydrochalcones [PK1212]
Löslichkeit1 mg/mL at 22 °CDMSO (Slightly), Methanol (Slightly)
Endocrine DisruptorsPotential endocrine disrupting compound
Schmelzpunkt110.0 °C113-114 °C(lit.)
Physical DescriptionOff-white powder[ChromaDex MSDS]Solid
Collision Cross Section194.4 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]192.5 Ų [M+H]+ [CCS Type: TW
Siedepunkt468.89°C (rough estimate)
Dichte1.3178 (rough estimate)
Brechungsindex-54 ° (C=3.2, 95% EtOH)
LagerbedingungenKeep in dark place,Sealed in dry,Room Temperature
AggregatzustandSolid
pKa (Säurekonstante)7.15±0.40(Predicted)
FarbeLight Yellow to Tan
Merck14,7327
Hauptanwendungenfood and beverages
Kosmetik-Inhaltsstoffe FunktionenSKIN CONDITIONING
InChIKeyIOUVKUPGCMBWBT-LKLLPNDVNA-N
SMILESC(C1C(=CC(O)=CC=1O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)(=O)CCC1C=CC(O)=CC=1 |&1:9,10,11,13,15,r|
LogP (Verteilungskoeffizient)0.452 (est)
CAS Datenbank60-81-1(CAS DataBase Reference)
EPA chemische InformationenPhlorizin (60-81-1)

Sicherheit & Vorschriften

GefahrenübersichtIntraperitoneal
F3-10-23
Wassergefährdungsklasse (WGK)3
Zollcode29389090
RTECS-Nr.UC2080000
R-Sätze (R)36/37/38
GefahrensymboleXi
Sicherheitshinweise (S)26-36
Lagerklasse11 - Combustible Solids

Anwendungen & Verwendung

Verwenden

Sodium-glucose cotransporter 1 (SGLT1) is a high affinity, low capacity transporter abundant in the small intestine, with some expression in the kidney as well. SGLT2 is a low affinity, high capacity transporter in the kidney that accounts for approximately 90% of glucose reabsorption into the blood stream. Selective inhibition of SGLT2 is a potential strategy for reducing plasma glucose levels as a treatment for diabetes. Phlorizin is a natural product, first isolated from the bark of apple trees, that reduces plasma glucose levels by blocking renal and intestinal glucose absorption through inhibition of SGLT1 and SGLT2. It competitively inhibits the initial rate of a-methyl-D-glucopyranoside (a-MDG) uptake in human COS-1 cells expressing hSGLT1 and hSGLT2 with IC50 values of 400 and 65 nM, respectively. In HEK293T cells expressing human SGLT1 and SGLT2, phlorizin exhibits Ki values of 140 and 11 nM, respectively, at 37°C.